A versatile post-synthetic method on a solid support for the synthesis of RNA containing reduction-responsive modifications. Issue 29 (30th June 2016)

• Record Type: Journal Article
• Authors: Biscans, Annabelle; Rouanet, Sonia; Vasseur, Jean-Jacques; Dupouy, Christelle; Debart, Françoise
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 29(2016)
• Page Start: 7010
• Page End: 7017
• Publication Date: 2016-06-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01272h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : This work describes a novel post-synthetic method on a solid support to introduce various disulfide bond-containing groups at 2′-OH of oligoribonucleotides. Abstract : An original post-synthetic method on a solid support was developed to introduce various disulfide bond containing groups at the 2′-OH of oligoribonucleotides (RNAs). It is based on a thiol disulfide exchange reaction between several readily accessible alkyldisulfanyl-pyridine derivatives and 2′- O -acetylthiomethyl RNA in the presence of butylamine. By this strategy, diverse 2′- O -alkyldithiomethyl RNAs were obtained. These modifications provided high nuclease resistance to RNA and were easily removed with glutathione treatment, thus featuring a potential use for siRNA prodrugs.